CIS-1,2-CYCLOOCTANEDIOL

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclooctene (4.41 g) was dissolved in acetonitrile (45 ml) and water (15 ml), and to the solution N-methylmorpholine N-oxide (5.15 g) and microcapsulated osmium tetroxide (1 g, containing 10% osmium tetroxide) were added, and the mixture was stirred at 40 to 50° C. for 21 hours. Insoluble microcapsulated osmium tetroxide was removed by filtration, and washed with acetonitrile, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound (4.97 g). Insoluble microcapsulated osmium tetroxide was removed by filtration washed with acetonitrile the filtrate was concentrated under reduced pressure The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclooctene (4.41 g) was dissolved in acetonitrile (45 ml) and water (15 ml), and to the solution N-methylmorpholine N-oxide (5.15 g) and microcapsulated osmium tetroxide (1 g, containing 10% osmium tetroxide) were added, and the mixture was stirred at 40 to 50° C. for 21 hours. Insoluble microcapsulated osmium tetroxide was removed by filtration, and was washed with acetonitrile, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound (4.97 g) as a colorless solid. Insoluble microcapsulated osmium tetroxide was removed by filtration was washed with acetonitrile the filtrate was concentrated under reduced pressure The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclooctene (4.41 g) was dissolved in acetonitrile (45 ml) and water (15 ml), and to the solution N-methylmorpholine N-oxide (5.15 g) and microcapsulated osmium tetroxide (1 g, containing 10% osmium tetroxide) were added, and the mixture was stirred at 40 to 50° C. for 21 hours. Insoluble microcapsulated osmium tetroxide was removed by filtration, and was washed with acetonitrile, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound (4.97 g) as a colorless solid. Insoluble microcapsulated osmium tetroxide was removed by filtration was washed with acetonitrile the filtrate was concentrated under reduced pressure The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclooctene (4.41 g) was dissolved in acetonitrile (45 ml) and water (15 ml), and to the solution N-methylmorpholine N-oxide (5.15 g) and microcapsulated osmium tetroxide (1 g, containing 10% osmium tetroxide) were added, and the mixture was stirred at 40 to 50° C. for 21 hours. Insoluble microcapsulated osmium tetroxide was removed by filtration, and was washed with acetonitrile, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound (4.97 g) as a colorless solid. Insoluble microcapsulated osmium tetroxide was removed by filtration was washed with acetonitrile the filtrate was concentrated under reduced pressure The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 262 ml of aqueous NaIO4 was added drop wise to a vigorously stirred suspension of 105 g chromatographic grade silica gel in 500 ml dichloromethane whereby a white suspension was formed. To the suspension a solution of 6.1 g cis-1,2-cyclo-octanediol in 100 ml dichloromethane was added. The reaction mixture was stirred over night at room temperature, after which the mixture was filtered whereby the residue was washed 3 times with 100 ml dichloromethane. Finally the filtrate was dried over NaSO4, after which the solvent was removed under reduced pressure. was formed after which the mixture was filtered whereby the residue was washed 3 times with 100 ml dichloromethane Finally the filtrate was dried over NaSO4 after which the solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 262 ml of aqueous NaIO4 was added drop wise to a vigorously stirred suspension of 105 g chromatographic grade silica gel in 500 ml dichloromethane whereby a white suspension was formed. To the suspension a solution of 6.1 g cis-1,2-cyclo-octanediol in 100 ml dichloromethane was added. The reaction mixture was stirred over night at room temperature, after which the mixture was filtered whereby the residue was washed 3 times with 100 ml dichloromethane. Finally the filtrate was dried over NaSO4, after which the solvent was removed under reduced pressure. was formed after which the mixture was filtered whereby the residue was washed 3 times with 100 ml dichloromethane Finally the filtrate was dried over NaSO4 after which the solvent was removed under reduced pressure

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclooctene (4.41 g) was dissolved in acetonitrile (45 mL) and water (15 mL), and to the solution were added N-methylmorpholine N-oxide (5.15 g), microencapsulated osmium tetraoxide (1 g, 10% osmium tetraoxide content), followed by stirring at 40-50° C. for 21 hours. Any insoluble microencapsulated osmium was filtered off, and was washed with acetonitrile. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel flash column chromatography (hexane:ethyl acetate=1:1), to thereby give the title compound (4.97 g). Any insoluble microencapsulated osmium was filtered off was washed with acetonitrile The filtrate was concentrated under reduced pressure the residue was purified by silica gel flash column chromatography (hexane:ethyl acetate=1:1)

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclooctene (4.41 g) was dissolved in acetonitrile (45 ml) and water (15 ml), and to the solution N-methylmorpholine N-oxide (5.15 g) and microcapsulated osmium tetroxide (1 g, containing 10% osmium tetroxide) were added, and the mixture was stirred at 40 to 50° C. for 21 hours. Insoluble microcapsulated osmium tetroxide was removed by filtration, and washed with acetonitrile, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound (4.97 g). Insoluble microcapsulated osmium tetroxide was removed by filtration washed with acetonitrile the filtrate was concentrated under reduced pressure The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclooctene (4.41 g) was dissolved in acetonitrile (45 ml) and water (15 ml), and to the solution N-methylmorpholine N-oxide (5.15 g) and microcapsulated osmium tetroxide (1 g, containing 10% osmium tetroxide) were added, and the mixture was stirred at 40 to 50° C. for 21 hours. Insoluble microcapsulated osmium tetroxide was removed by filtration, and washed with acetonitrile, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound (4.97 g). Insoluble microcapsulated osmium tetroxide was removed by filtration washed with acetonitrile the filtrate was concentrated under reduced pressure The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclooctene (4.41 g) was dissolved in acetonitrile (45 ml) and water (15 ml), and to the solution N-methylmorpholine N-oxide (5.15 g) and microcapsulated osmium tetroxide (1 g, containing 10% osmium tetroxide) were added, and the mixture was stirred at 40 to 50° C. for 21 hours. Insoluble microcapsulated osmium tetroxide was removed by filtration, and was washed with acetonitrile, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound (4.97 g) as a colorless solid. Insoluble microcapsulated osmium tetroxide was removed by filtration was washed with acetonitrile the filtrate was concentrated under reduced pressure The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclooctene (4.41 g) was dissolved in acetonitrile (45 ml) and water (15 ml), and to the solution N-methylmorpholine N-oxide (5.15 g) and microcapsulated osmium tetroxide (1 g, containing 10% osmium tetroxide) were added, and the mixture was stirred at 40 to 50° C. for 21 hours. Insoluble microcapsulated osmium tetroxide was removed by filtration, and was washed with acetonitrile, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound (4.97 g) as a colorless solid. Insoluble microcapsulated osmium tetroxide was removed by filtration was washed with acetonitrile the filtrate was concentrated under reduced pressure The residue was purified by flash column chromatography on silica gel (hexane:ethyl acetate=1:1)